5-(2-Pyridyl)oxazole → 1-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-phenoxyphenyl)propane

HRID 386434Notes

Reaction equation

HRID 386434 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][CH:10]=[N:9][CH:8]=1.[O:12]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](O)=[O:28])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:28]=[C:27]([C:10]1[O:11][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][N:9]=1)[CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 7371945-(2-Pyridyl)oxazoleHCID 220365723-(4-Phenoxyphenyl)propanoic acid

Product 1

HCID 167351611-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-phenoxyphenyl)propaneYield 37%

Procedure

The title compound (11f) was prepared from 5-(2-pyridyl)oxazole and 3-(4-phenoxyphenyl)propanoic acid (S30) using General Procedure B. PTLC (SiO2, 50% EtOAc-hexanes) afforded 11f (83 mg, 0.22 mmol, 37%) as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) 8.69 (m, 1H), 7.89-7.86 (m, 2H), 7.82 (td, 1H, J=7.8, 1.8 Hz), 7.34-7.30 (m, 3H), 7.24 (d, 2H, J=8.5 Hz), 7.10-7.07 (m, 1H), 6.98 (d, 2H, J=12.1 Hz), 6.94 (d, 2H, J=8.6 Hz), 3.47 (t, 2H, J=7.4 Hz), 3.10 (t, 2H, J=7.4 Hz); 13C NMR (CDCl3, 100 MHz) 187.2, 157.4, 157.1, 155.5, 153.3, 150.1, 146.2, 137.1, 135.2, 129.7, 129.6, 126.9, 124.1, 123.0, 120.4, 119.1, 118.6, 40.7, 29.0; IR (film) νmax 3055, 2930, 1698, 1589, 1504, 1488, 1425, 1380, 1237, 1167, 1065, 871, 784, 692 cm−1; ESI-TOF m/z 371.1388 (C23H18N2O3+H+ requires 371.1396).

Sources & evidence

ORD record
ord-0eb0c472e6fb4996acb2fe9824c6fe9d
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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